从带有 4-吡喃酮单元的喹喔啉制备苯并[a]吡喃并[3,2-c]吩嗪-4-酮的光化学方法

IF 2 3区 化学 Q2 CHEMISTRY, ORGANIC Journal of Heterocyclic Chemistry Pub Date : 2024-06-22 DOI:10.1002/jhet.4861
Dmitry V. Tsyganov, Andrey N. Komogortsev, Valeriya G. Melekhina, Artem N. Fakhrutdinov, Boris V. Lichitsky
{"title":"从带有 4-吡喃酮单元的喹喔啉制备苯并[a]吡喃并[3,2-c]吩嗪-4-酮的光化学方法","authors":"Dmitry V. Tsyganov,&nbsp;Andrey N. Komogortsev,&nbsp;Valeriya G. Melekhina,&nbsp;Artem N. Fakhrutdinov,&nbsp;Boris V. Lichitsky","doi":"10.1002/jhet.4861","DOIUrl":null,"url":null,"abstract":"<p>Photochemical properties of terarylenes with quinoxalines bridge unit and allomaltol fragment was investigated. We have demonstrated that starting compounds with hydroxyl group in 3-hydroxy-4-pyranone substituent does not undergo any photoinduced transformations. Wherein, conversion to methoxy derivatives allows one to realize photochemical 6π-electrocyclization for considered quinoxalines. Based on data of x-ray analysis the observed difference in reactivity is connected with the presence of hydrogen bond in hydroxyl derivatives. As a result of carried out research photochemical approach to novel benzo[<i>a</i>]pyrano[3,2-<i>c</i>]phenazin-4-ones was implemented.</p>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 9","pages":"1387-1398"},"PeriodicalIF":2.0000,"publicationDate":"2024-06-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photochemical method for preparation of benzo[a]pyrano[3,2-c]phenazin-4-ones from quinoxalines with 4-pyranone unit\",\"authors\":\"Dmitry V. Tsyganov,&nbsp;Andrey N. Komogortsev,&nbsp;Valeriya G. Melekhina,&nbsp;Artem N. Fakhrutdinov,&nbsp;Boris V. Lichitsky\",\"doi\":\"10.1002/jhet.4861\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Photochemical properties of terarylenes with quinoxalines bridge unit and allomaltol fragment was investigated. We have demonstrated that starting compounds with hydroxyl group in 3-hydroxy-4-pyranone substituent does not undergo any photoinduced transformations. Wherein, conversion to methoxy derivatives allows one to realize photochemical 6π-electrocyclization for considered quinoxalines. Based on data of x-ray analysis the observed difference in reactivity is connected with the presence of hydrogen bond in hydroxyl derivatives. As a result of carried out research photochemical approach to novel benzo[<i>a</i>]pyrano[3,2-<i>c</i>]phenazin-4-ones was implemented.</p>\",\"PeriodicalId\":194,\"journal\":{\"name\":\"Journal of Heterocyclic Chemistry\",\"volume\":\"61 9\",\"pages\":\"1387-1398\"},\"PeriodicalIF\":2.0000,\"publicationDate\":\"2024-06-22\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Heterocyclic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/jhet.4861\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Heterocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/jhet.4861","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

摘要

我们研究了带有喹喔啉桥单元和异麦芽酮醇片段的萜烯类化合物的光化学特性。我们已经证明,3-羟基-4-吡喃酮取代基中含有羟基的起始化合物不会发生任何光诱导转化。在这种情况下,转化为甲氧基衍生物可以使考虑的喹喔啉类化合物实现光化学 6π 电环化。根据 X 射线分析数据,观察到的反应性差异与羟基衍生物中存在氢键有关。作为研究成果,我们采用光化学方法制备了新型苯并[a]吡喃并[3,2-c]酚嗪-4-酮。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
Photochemical method for preparation of benzo[a]pyrano[3,2-c]phenazin-4-ones from quinoxalines with 4-pyranone unit

Photochemical properties of terarylenes with quinoxalines bridge unit and allomaltol fragment was investigated. We have demonstrated that starting compounds with hydroxyl group in 3-hydroxy-4-pyranone substituent does not undergo any photoinduced transformations. Wherein, conversion to methoxy derivatives allows one to realize photochemical 6π-electrocyclization for considered quinoxalines. Based on data of x-ray analysis the observed difference in reactivity is connected with the presence of hydrogen bond in hydroxyl derivatives. As a result of carried out research photochemical approach to novel benzo[a]pyrano[3,2-c]phenazin-4-ones was implemented.

求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Journal of Heterocyclic Chemistry
Journal of Heterocyclic Chemistry 化学-有机化学
CiteScore
5.20
自引率
4.20%
发文量
177
审稿时长
3.9 months
期刊介绍: The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.
期刊最新文献
Issue Information Issue Information Palladium-Catalyzed Synthesis of Pyrrolo[1,2-α]Pyrazines From N-Phenacyl Pyrrole-2-Carbonitriles and Aryl Boronic Acids Synthesis and Anticancer Evaluation of Tryptanthrin-1,2,3-Triazole Hybrids Syntheses of 2,4-Substituted Quinazolines via One-Pot Three-Component Reactions Based on Manganese Dioxide/tert-Butyl Hydrogen Peroxide Co-Oxidation Using Alcohols
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1